Triethylamine → Ethyl (pyrimidin-5-yl)acetate

HRID 2294940Notes

Reaction equation

HRID 2294940 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[CH:4]=[N:3][CH:2]=1.[CH2:11](N(CC)CC)[CH3:12].ClC(OCC)=O>C(Cl)Cl.CN(C)C1C=CN=CC=1.[Cl-].[NH4+]>[N:1]1[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]=[N:3][CH:2]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 21471675(Pyrimidin-5-yl)acetic acid

Product 1

HCID 21471619Ethyl (pyrimidin-5-yl)acetateYield 81.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4.06 g of 5-pyrimidineacetic acid (F. Zymalkowski and E. Reimann, Arch. Pharm. 1966 299 362-7) and triethylamine (6.55 g) in methylene chloride (150 mL) at 0° C. was added ethyl chloroformate (6.38 g) followed by 4-dimethylaminopyridine (0.72 g). The mixture was stirred at 0° C. for 1 h, then the solution was diluted with methylene chloride (200 mL) and saturated ammonium chloride (150 mL) was added. After removal of the organic phase, the aqueous layer was extracted with methylene chloride (2×200 mL) and the combined organic extracts were dried over MgSO4 and concentrated to give 7.33 g of a crude oil. Purification by column chromatography, eluting with hexane; 50% ethyl acetate gave ethyl 5-pyrimidinylacetate (3.98 g) as a colorless oil.

Workup

  1. additionwas added
  2. customAfter removal of the organic phase
  3. extractionthe aqueous layer was extracted with methylene chloride (2×200 mL)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customto give 7.33 g of a crude oil
  7. customPurification by column chromatography
  8. washeluting with hexane

Sources & evidence

ORD record
ord-1d9df74b87634c6dbb12f57360d0cf1b
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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